The Best Boot Trend to Wear With Skirts and Dresses, Per Bella Hadid

Bella Hadid knows how to put an outfit together. This is very clear. So she's always a good person to look to when you want to know how to style a particular piece. Case in point: Hadid was out in New York over the weekend, and the early-fall-outfit vibes were in full force. She wore an eclectic mix that included a colorful striped cardigan, a tank top, a pleated miniskirt, and boots. It was an early 2000s dream of a look.
Speaking of boots, 'tis (almost) the season to wear them again, and we're taking notes for future reference. In case you have been pondering what style to wear with skirts and dresses, look no further than here. Hadid styled her miniskirt with chunky knee-high boots, making for the perfect transitional summer-to-fall look. Scroll for outfit inspiration and to shop our favorite chunky knee-high boots to wear with skirts and dresses.
On Bella Hadid: Comme des Garçons sweater; Killah skirt; Betsey Johnson Betseyville Taxi Bag; Prada boots; Emi Jay Big Effing Clip ($35); Vogue Eyewear VO5315S Sunglasses ($111)
Shop Chunky Knee Boots
Next up, 21 New Ankle Boots That'll Sell Out by October
Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
Spotted in Midtown NYC: The Blazer Trend Elegant Dressers Will Wear With Jeans This Spring
I feel strongly about this.
By Allyson Payer
-
10 Who What Wear Editors, 64 Spring Buys—Inside Our Seasonal Mood Boards
Everything inspiring our wardrobes this season.
By Anna LaPlaca
-
Anti–Skinny Jeans Are Still Ruling in 2025—Finally, 15 Fresh Ways to Wear Them
Stealing these looks this season.
By Michelle Scanga
-
From Prada to COS—Here's Everything I Packed and Wore for Milan Fashion Week
A full breakdown.
By Eliza Huber
-
Amal Clooney's Croc-Embossed Thigh-High Boots Are About to Cause a Stir
Guaranteed.
By Erin Fitzpatrick
-
I Already Have an Elevated Closet, But If I Were to Start Over, I'd Go for These 5 Staples
Effortless outfit ideas ahead.
By Jennifer Camp Forbes
-
These 5 Inspiring Outfits Are Proof You Can Easily Merge Classic and Trendy Styles
Trust me, you're going to want to re-create these looks.
By Jennifer Camp Forbes
-
The Boot Trend Everyone With Expensive Taste Is Styling Instead of Flats or Heels
We're here for it.
By Michelle Scanga